Ethanol → 2,3-dihydro-7-methoxy-8-[4-(4-phenyl-1-piperazinyl)butyloxy]cyclopenta[c][1]benzopyran-4(1H)-one

HRID 22339Notes

Reaction equation

HRID 22339 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([O:25][CH3:26])=[CH:13][C:14]2[O:19][C:18](=[O:20])[C:17]3[CH2:21][CH2:22][CH2:23][C:16]=3[C:15]=2[CH:24]=1)(=O)=O.[C:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)C.C([O-])(=O)/C=C/C([O-])=O>CC(C)=O>[CH3:26][O:25][C:12]1[C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][N:36]2[CH2:37][CH2:38][N:33]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:34][CH2:35]2)=[CH:24][C:15]2[C:16]3[CH2:23][CH2:22][CH2:21][C:17]=3[C:18](=[O:20])[O:19][C:14]=2[CH:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 70961-PhenylpiperazineHCID 5460307FumarateHCID 199276342,3-dihydro-8-[4-(methanesulfonyloxy)butyloxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one

Product 1

HCID 199276422,3-dihydro-7-methoxy-8-[4-(4-phenyl-1-piperazinyl)butyloxy]cyclopenta[c][1]benzopyran-4(1H)-oneYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Method B (16 h at 80° C.); starting materials: 2,3-dihydro-8-[4-(methanesulfonyloxy)butyloxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one (example 84) and 1-phenylpiperazine; yield 55%; fusion point 162°-165° C. (from ethanol). Fumarate: method E; yield 95%; fusion point 179°-183° C. (from acetone).

Workup

  1. customMethod B (16 h at 80° C.)

Sources & evidence

ORD record
ord-96490beb0f534cc89f51d29988f58252
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

Loading…